Daring Hallow's Night
by Warlordess
Summary: Belated Halloween one-shot written for prompt fulfillment on Tumblr. Everyone seems to know how Ash feels about her except for the man in question himself. Luckily Brock has a trick up his sleeve to move things along... Misty can only hope that the end of the night bears a treat or two as well. Pokeshipping. Probably one of my last fanfics, folks.


**Disclaimer** \- I own nothing! Just your average klepto hellbent on stealing my fave OTP characters and forcing them to do what I say!

 **Author** \- Warlordess

 **Notes** \- This was written in response to a request prompt on Tumblr. Awhile back I'd asked my readers to send in one-word-prompts for me to fulfill since I now work nights at a job where it's mostly just sitting around and waiting for time to pass. Someone sent in 'Halloween' and just in time for the holiday to be only a day or few away! So I whipped this up real quick... Unfortunately, I forgot to post it anywhere except for on Tumblr.

 **Extra note** \- Due to massive lack of reader response, I am notifying the few who bother to read my fics that I will probably not be posting many more of them after this. I plan on updating all site I post on with more or less the same works but then I will be withdrawing from sharing my future works with anyone. I have asked and begged and pleaded and reasoned over the fact that the fandom has changed and is more diverse and yet... I basically break my own heart when I post something nowadays only to receive maybe one or two comments... So I think it's best to call it quits so I don't keep disappointing myself. It's been a blast, guys, but yeah. I refuse to keep begging for scraps.

 **O** o **O** o **O**

 **Title** \- "Daring Hallow's Night"

 **Summary** \- Everyone seems to know how Ash feels about her except for the man in question himself. Luckily Brock has a trick up his sleeve to move things along... Misty can only hope that the end of the night bears a treat or two as well.

 **O** o **O** o **O**

"Why is this happening to me…?" a young man with jet black wild hair wailed in woe, looking at her fussing at her reflection in the mirror from behind.

"To us, Ash, to _us_. And if you hadn't of chickened out and just _told_ Brock that you liked me during truth-or-dare, he wouldn't have forced us to do this instead.

"In fact, I honestly _should_ be blaming you for dragging me into this _but_ ," the redhead paused, sighed, placed one last delicate pin into her hair to hold together the long ponytail of red draping down her back, and grinned, "I _do_ look good so I guess I can let it go."

Ash stared at her from his position by the bathroom door, taking in the sight of her bright hair french braided along either side of her scalp until it reached the aforementioned ponytail extension; light touches of mascara, eye liner, concealer, and lip gloss highlighting her facial features and making the teal of her eyes and the pink of her lips pop just right. A (fake) diamond bangle sat delicately on her one wrist, drawing attention from her somewhat wiry, lanky frame; a long sweeping pale yellow gown fluttering down around her every subtle curve, layers of pink rose motif and white accenting it just so while a blue sash contrasted with the color scheme around her torso.

"I… I don't like you," Ash denied, licking his mysteriously chapped lips and blinking his eyes rapidly to pull himself away from her odd, unyielding charm. He couldn't find it in himself to reject the other half of her statement.

"Honestly, Ash," Misty huffed dramatically with a roll of her eyes as she stopped admiring herself and turned to face him, "the blushing, angry, obstinate rejection was alright - maybe even cute - when we were kids, but now? C'mon, already. I'm not gonna wait forever."

" _You're_ not–"

Honestly, that sounded more like a personal problem to him but he wasn't going to walk further into her trap.

"–Look, I don't wanna talk about this anymore, Misty. Just tell me one thing; who the heck am I supposed to be?" he asked instead, stepping further into the center of the room and under brighter lighting so that his scrutiny would seem more obvious and recognizable.

"Ash, you're Dimitri from that old kids movie, Anastasia!" she responded indignantly, clearly upset that he didn't already know this. "You know, he was a castle servant who helped the Princess Anastasia - that's _me_ \- escape death during the people's' riots of St. Petersburg, Russia."

"… Oooh, and _why_ were they rioting again?" he asked her next. "And what makes my character so important?"

"Aaagh… The riots were because of Rasputin's curse on the royal Romanov family, and you're important because of how Anya - _Anastasia_ \- and Dimitri reconnect later on. Seriously, Ash, am I just going to have to explain the whole movie to you?"

"That might be a good idea, yeah."

Misty rolled her eyes again and sat down quite carefully on the closed toilet seat lid, gesturing for her friend to join her by sitting on the swell of the bathtub. After he did so, she gave a cliff notes synopsis of the film in question and, when she was through, she opened up the floor for his final questions.

"So… so I'm this Dimitri guy who, as a kid, helped you - Princess Anastasia, who goes by Anya as an orphaned, amnesiac adult - escape certain death from the cursed riots of the citizens of Russia. Then, later on, we meet again because my guy is a scam artist and I've got papers that'll get your character to Paris which, despite you forgetting everything about your family for a good decade, you conveniently know you need in order to maybe find the very same grandmother - your only family - that I'm planning to scam money from.

"Wow," Ash interrupted his own understanding of the plot to say, "my character's a jerk, huh?"

"Yeah, that's why I thought it'd be a nice fit," the redhead replied smartly.

"Hey!"

"Oh, c'mon, Ash. I'm kidding… mostly," and then, before he could object again, "And it's not like Dimitri goes through with it. After using the woman he's in love with, he realizes he's actually helped her find the family she so desperately needed and he bows out without taking the money."

"… Wait a sec, what was that last part?"

"He leaves without taking the money?"

"No, before that."

"He isn't heartless enough to go through with his scam?"

"Misty, you just said that my character is in love with yours!" The raven-haired boy leapt to his feet in shock, "Why'd you even pick these characters?!"

"Because, after _you_ were told during truth-or-dare to admit you had feelings for me and _you_ said _you_ wouldn't do it, Brock had to pick something else to dare _you_ to do! And _then_ , after he said we had to wear matching costumes to the party, you told me - and I quote - to _just pick whatever_ because you're no good at this kind of stuff. Well, it sucks to be you because I love this movie and it's too late to change it up now!"

"B - but - but Misty, I…" he tapered off. Far be it for him to outright claim he's incapable of doing something but this felt like another trap, and one that he'd walked right into.

"Look, I'm not gonna force you, Ash; I can't do that. But if it were _me_ in this predicament - and thanks to you, it kind of _is_ \- I'd want to just suck it up and get through the night. So I guess the choice is yours. Do you want to just do whatever you can to get through this one night with my help _or_ do you want to be ridiculed by all of our friends for being a coward while Brock thinks up something else - something probably _worse_ \- for you to do next time?"

The two of them were both on their feet once more, staring each other down quite intensely. Ash broke eye contact first with a long-suffering sigh, looking equally brave yet unwilling.

"Fine, but no mushy stuff," he told her in the end, "And I still don't know why I'm wearing _this_ ," he paused and swept his arms open dramatically at his rather plain costume of pale green casual-dress collared shirt, brown trousers with a uniform belt, and a bolder green vest, "and you get to wear _that_. Doesn't seem much like matching outfits to me."

"Yeah, but they're from the same scene," she told him with a nonchalant shrug of her shoulders.

"Now c'mon, Ash, we're already late getting to the lab. Brock's gotta see us together in costume _and_ interacting before he'll consider the dare completed."

He did his best to keep his eyes off of her the entire way there, though he did end up enlisted to help hold up her dress while they walked to prevent it from getting dirty, but yeah, other than that, he did what he could to ignore the clustered, agitated fluttering in his stomach, the flustered warning bells going off in the back of his head.

 _I'm not gonna wait forever_ , her resigned tone resounded in his head, and he admitted to himself that she sounded almost pained, but he didn't have it in him - whatever _it_ was - to pursue more answers or resolutions on the subject.

 _I don't like you_ , he had replied at the time, doing his best to convince himself as well without a shadow of a doubt. _I don't like her_ , he thought with renewed force this time, staring avidly at her back as she walked before him.

Or maybe that was because he couldn't take his eyes off of her, and such a thing greatly frustrated him.

Being enamored with a childhood friend, someone he couldn't shake off completely and distance himself from, deeply shook him. Or else it would have if that was definitely the case, but he told himself it wasn't.

And bless his ignorance, for it was truly as blissful as they always claimed it to be.

"Oh my goodness, Misty, honey, you look great!" Delia fawned at the redheaded young woman almost ten minutes later after the two of them finally arrived at their destination. "And I see you did quite a good job cleaning my son up too!"

"Thanks, Mrs. Ketchum, my sisters helped a lot with the costumes. I'll let them know how much you like their work when I go back home."

Oh, yeah, he'd forgotten that Misty had only come to town because she'd been invited to Professor Oak's annual Halloween party, just like all of his other friends who'd met his mentor at some point. It was oddly relieving to know that she'd be out of his hair sometime within the next few days and that he'd then be in the clear. Now he just had to make it that far first.

The comments didn't stop with his mom, though. May and Dawn both had plenty of positive things to say, and even Tracey said he was interested in sketching them in costume at some point if they were willing (also adding that they could dress up Pikachu as Pooka, though Ash didn't recognize who he was talking about since Misty had left any animals out of her synopsis of the movie). However there were also others who weren't as receptive.

Gary, as a for instance, couldn't help himself from laughing and telling Ash how whipped he must have been to give so easily into Misty's demands (whatever that meant). Bayleef, for whatever reason, was putting up quite a fight about the two of them standing so close to one another and being lumped together as a pair by everyone they happened across.

Overall though, reception was positive, and Brock had only one complaint when they finally got around to showing off to him…

"You did great, Ash. I'm impressed! But just dressing up doesn't help you play the part so you need to do something in-character for me to consider the dare fulfilled."

"Something… well, wha'd'ya want, Brock? Because I've never seen the movie and the only real thing I know this Dimitri tries to do is steal money from _her_ ," he paused to jack his thumb in Misty's direction, "family. And I'm not walking all the way to Cerulean City just to pretend to scam her sisters."

"No, you don't need to do anything that big… or illegal. But, Misty, don't you remember about that dance Anya and Dimitri shared on the boat while he was training her to play her part as the princess? And they did something like it again at the end of the movie."

"You want me t - to _dance_? With _her_? _Here_?!" the raven-haired trainer asked, his tone pitching an octave higher for every addition to his inquire.

"What's it really matter, Ash? You two have danced once before, haven't you?" the Pokemon doctor-in-training responded skeptically with a raised eyebrow.

"B - but not with all these p - people that we _know_ around!" Ash defended obstinately as he turned to look at them all. And then he rounded on Misty, who'd been pretty quiet since their final challenge had been brought up. "What about you, Myst? You told me earlier that you'd basically been dragged into all this, right?"

Misty stared evenly down the bridge of her nose at him for a few seconds before making her decision.

"Yeah… but I also said that I love this movie, so why would I pass up a chance to reenact a scene from it? Plus, like Brock said, we've danced together before, right? No big deal, Ash; and, after this, you're done. It's not like he's asking for much, is he?"

"B - but he - I - I mean, what about–"

"–Great! Problem settled! Here we go!" she finished confidently, grabbing one of his hands and dragging him out to the center of the room against his will, lacing fingers with him while her other hand latched onto his and tugged it towards the small of her back, holding it in place for a few seconds.

Ash felt panic and… something _else_ … well up unabated, unexpected, within him at the very real concept of touching her so intimately. Their more traditional dance from when they were kids had allowed for more physical distance between them than this.

Oh, what he wouldn't give to go back to those days… But, then again, would he give anything? The two of them were in a really good place now, the best of friends even, despite some mixed signals of _maybe more_ and miscommunication here and there. It was pretty unreasonable of him to wish and want to return to a time when they two of them barely even got along at all.

And yet, there was an overwhelming sense of longing he felt quaking his mind and breaking his heart and dehydrating his sense of comfort, evaporating it into nothing. And he wasn't sure what to do about it, or even if it was worth doing anything at all because, while it confused him - scared him even, though he'd never admit it out loud - it also… he couldn't explain it beyond the fact that it… _excited_ him.

"Ash, I'm alright with leading but, you know… you've gotta at least pretend to play along," his redheaded dance partner admonished him disappointingly, inadvertently yanking him to her left and into a sweeping twirly move he hadn't known before that she was able to pull off.

"Mwah! I - I mean, uh… okay, so… what do I do?"

"Well, what do you _want_ to do?"

He didn't know. He wanted to get out of this dare, out of these clothes, out of their dance, out of his situation. He wanted to ask Misty why she didn't seem so bothered by being forcibly involved in his predicament despite claiming earlier how much trouble it seemed to bring her. He wanted to ask her what she meant by not being willing to wait forever - _wait for what?_ He couldn't help but adamantly deny - and where her bravery came from, to be able to just… willingly admit that there was something extra there between them…

Oh.

 _Between_ them.

And that's when Ash Ketchum's conscious reality altered forever.

He looked her up and down in her extravagant glittering costume gown and tiara, looked at the faint sweat on her brow, the enthused smile lighting up her face, his own enamored expression reflecting in her eyes, and he realized he'd been wrong before.

You just couldn't be this conscious of someone without it meaning something; without it meaning _everything_.

"I wanna," he faltered to lick his dry lips for the second time that night, only this time was less out of primal attraction and more out of over-eagerness to share with her what he knew without a doubt, "... I wanna tell you that I like you."

"Wow, really, Ash?" she asked him with an exaggerated gasp, stopping mid-motion to give him her full attention. "I can't believe it!"

"Yeah, okay, Misty."

"I mean, are you really sure though? I wouldn't want you getting sucked up into the heat of the moment of Brock's dare or anything! I know you said earlier that you didn't have any feelings like that for me at all. No mushy stuff, you said, right?"

"Yeah, yeah; yuck it up while you can."

"I'm just saying, I wouldn't want there to be a mistake or–"

"–Misty, I get it, okay? I'm an idiot. I was the last one in the _world_ to figure it out. Point taken."

He cleared his throat and stared at her with his lips puckered a bit and arms crossed in agitation.

"So, do you like me back?" he asked then, highly exasperated by her sarcastic reaction to his confession. Unfortunately, the torture wasn't over yet. To be fair, he already knew the answer to the question, but there was no harm in receiving verbal confirmation.

"Oh, Ash, let's be realistic. If I gave it away so easily, how would that be any fun for me?"

But then, ignoring his affronted and rejected silence, she slung both of her arms around his neck and pulled him so close to her that their noses were barely three inches apart.

"Now answer me this, Mr. Pokemon Master…" And, with a cheshire grin illuminating her features in the semi-darkness, she whispered in his ear, "Would you like a trick or a treat for all of your hard work?"

Ash gulped, the anxious lump in his throat refusing to dissolve away entirely. He found it difficult to pick either choice, if he was being honest. And, to think, he was so sure he'd finally escaped these kinds of troubling either-or situations after making it through Brock's stupid dare…

But really, the torture was _just_ getting started.

 **O** o **O** o **O**

 **Notes** \- And that's all she wrote, folks! All kudos, favorites, shares, comments, etc, is appreciated! I need to be convinced to write anything new tbh, because it seems likes nobody ever has anything to say... So I guess that means my fics aren't worth saying anything about, meaning that they won't be missed if I choose to stop posting them...


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